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Fumonisin B₁

Cayman Chemical Item Number 62580

(CAS 116355-83-0)

Fumonisin B1 (CAS 116355-83-0)

See more	Ceramides/Sphingolipids (58) Lipids (176)

Description

Fumonisin B₁ is a mycotoxin produced from F. moniliforme, a prevalent fungus of corn and other grains. Outbreaks of food poisoning in livestock and humans following the consumption of Fusarium infested corn are caused by fumonisins.¹ It functions as an inhibitor of ceramide synthase (sphingosine N-acyltransferase).² Fumonisin B₁ attenuates the response of P388D1 cells to PAF and LPS by inhibiting ceramide formation.³ It also blocks the apoptotic response of HaCaT cells to the antiproliferative drug hexadecylphosphocholine, again through inhibition of ceramide production.⁴ Incubation of Swiss 3T3 cells with fumonisin B₁ results in both an altered cell morphology due to disruption of axonal growth and a decrease in cell proliferation.⁵

1 Gelderblom, W.C.A., Jaskiewicz, K., Marasas, W.F.O., et al. Fumonisins - novel mycotoxins with cancer-promoting activity produced by Fusarium moniliforme. Appl Environ Microbiol 54 1806-1811 (1988).

2 Wang, E., Norred, W.P., Bacon, C.W., et al. Inhibition of sphingolipid biosynthesis by fumonisins. Implications for diseases associated with Fusarium moniliforme. J Biol Chem 266 14486-14490 (1991).

3 Balsinde, J., Balboa, M.A., and Dennis, E.A. Inflammatory activation of arachidonic acid signaling in murine P388D1 macrophages via sphingomyelin synthesis. J Biol Chem 272 20373-20377 (1997).

4 Wieder, T., Orfanos, C.E., and Geilen, C.C. Induction of ceramide-mediated apoptosis by the anticancer phospholipid analog, hexadecylphosphocholine. J Biol Chem 273 11025-11031 (1998).

5 Meivar-Levy, I., Sbanay, H., Bershadsky, A.D., et al. The role of sphingolipids in the maintenance of fibroblast morphology. The inhibition of protrusional activity, cell spreading, and cytokinesis induced by fumonisin B₁ can be reversed by ganglioside GM3. J Biol Chem 272 1558-1564 (1997).

Formal Name	1,2,3-propanetricarboxylic acid, 1,-1'-[1-(12-amino-4,9,11-trihydroxy-2-methyltridecyl)-2-(1-methylpentyl)-1,2-ethanediyl] ester
CAS Number	116355-83-0
Molecular Formula	C₃₄H₅₉NO₁₅
Formula Weight	721.8
Formulation	A crystalline solid
Purity	≥98%
Stability	1 year
Storage	-20°C
Shipping	Room temperature in continental US; may vary elsewhere
SMILES	Copy SMILES to clipboard C[C@H](N)[C@@H](O)C[C@H](O)CCCC[C@@H](O)C[C@H](C)CC(OC(C[C@H](C(O)=O)CC(O)=O)=O)C(OC(C[C@@H](C(O)=O)CC(O)=O)=O)[C@@H](C)CCCC

Background Reading

Gelderblom, W.C.A., Jaskiewicz, K., Marasas, W.F.O., et al. Fumonisins - novel mycotoxins with cancer-promoting activity produced by Fusarium moniliforme. Appl Environ Microbiol 54 1806-1811 (1988).

Balsinde, J., Balboa, M.A., and Dennis, E.A. Inflammatory activation of arachidonic acid signaling in murine P388D1 macrophages via sphingomyelin synthesis. J Biol Chem 272 20373-20377 (1997).

Meivar-Levy, I., Sbanay, H., Bershadsky, A.D., et al. The role of sphingolipids in the maintenance of fibroblast morphology. The inhibition of protrusional activity, cell spreading, and cytokinesis induced by fumonisin B₁ can be reversed by ganglioside GM3. J Biol Chem 272 1558-1564 (1997).

Wieder, T., Orfanos, C.E., and Geilen, C.C. Induction of ceramide-mediated apoptosis by the anticancer phospholipid analog, hexadecylphosphocholine. J Biol Chem 273 11025-11031 (1998).

Wang, E., Norred, W.P., Bacon, C.W., et al. Inhibition of sphingolipid biosynthesis by fumonisins. Implications for diseases associated with Fusarium moniliforme. J Biol Chem 266 14486-14490 (1991).

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Fumonisin B1 is available in the following screening library:

Bio-active Lipid I Screening Library (96-Well)

Size	Price	Quantity	Subtotal
1 mg	$46.00		$0.00
5 mg	$207.00		$0.00
10 mg	$368.00		$0.00
50 mg	$1,610.00		$0.00
Bulk	Contact
		Cart Total	$0.00

Pricing updated 2012-05-26. Prices are subject to change without notice.

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Fumonisin B1